Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is €78
includes taxes & fees
27 May - 28 May
Clinton Motel
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (189 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is €122
includes taxes & fees
25 May - 26 May
Breakers Montauk
Seasonal outdoor pool, pool loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is €172
includes taxes & fees
3 Jun - 4 Jun
Ocean Resort Inn
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (474 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is €80
includes taxes & fees
4 Jun - 5 Jun
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, pool loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (497 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is €123
includes taxes & fees
26 May - 27 May
Aqualina Inn Montauk
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is €117
includes taxes & fees
10 Jun - 11 Jun
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (892 reviews)
  • cleanliness
    Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.
The price is €129
includes taxes & fees
27 May - 28 May
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (254 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is €510
includes taxes & fees
7 Jun - 8 Jun
Marram
Seasonal outdoor pool

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (701 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The price is €214
includes taxes & fees
26 May - 27 May
The Hampton Maid
Outdoor pool, pool umbrellas, pool loungers

Offshore Spa & Residences

Offshore Spa & Residences
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is €346
includes taxes & fees
26 May - 27 May
Offshore Spa & Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"G"
Kathleen 2-night trip
Posted 22 hours ago
Beachcomber Resort at Montauk

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Pier Blue Inn Old Saybrook - Essex: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. Montauk Yacht Club: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Hotel, 5-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and sunloungers.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Mashomack Preserve and Shell Beach during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.